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J Org Chem. 2010 Jul 2;75(13):4567-73. doi: 10.1021/jo100799x.

Synthesis and reactivity of 2H-pyran moiety in [60]fullerene cage skeleton.

Author information

1
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.

Abstract

The cyclopentadienyl type hexa-adduct C(60)(OOtBu)(6) 1 is readily converted into 2H-pyran containing fullerene derivative C(60)(O)(OOH)(OOtBu)(5) 2 in the presence of NaHCO(3) and hydroquinone. In the process, O-O bond of the tert-butylperoxo group on the central pentagon is cleaved, and the fullerene-bound oxygen radical inserts into a 5,6-junction to form the 2H-pyran moiety. Further reactions of 2 led to open-cage fullerenes with a nine-membered orifice and also both 3,4-dihydro-2H-pyran and 3,6-dihydro-2H-pyran containing fullerene derivatives. Mechanisms are proposed involving intramolecular S(N)2' and aza-Michael addition and ketal formation processes.

PMID:
20521834
DOI:
10.1021/jo100799x
[Indexed for MEDLINE]

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